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What Scares Entrepreneurs?

This article is more than 10 years old.

Halloween and entrepreneurship have much in common. Both require imagination and have a certain level of brashness. Both also have anchors in darkness and fear. Failure is the one fear we always hear about when talking about start-ups. But what else are those daring and passionate souls who launch enterprises afraid of? I put out a call to see what scares entrepreneurs. “Success” was a popular, if clichéd reply. (“Where do I go after I get to the top?) “Government” and “government interference” were more intriguing ones. Here are ten I found insightful:

(1) Losing my drive: Leila Janah founded Samasource, a non-profit that gets women, youth and refugees in the developing world technology-based jobs such as data-entry and call centers. It provides a livelihood to thousands, both in a paycheck and, more importantly, skills. She does it through “jugaad.” Jugaad, Leila tells me is a Hindi word that roughly means “doing more with less.” “As more people join Samasource and we secure new funding and better office space, I fear that we’ll lose our jugaad spirit and get complacent,” she says.

Born to parents from India, Leila learned about jugaad “whenever my brother and I asked for pocket money.” Her father would recite to them, “in a grand voice, a line borrowed from the poet Juvenal: ‘My children, luxury is more ruthless than war.’” It was his way of teaching Leila and her brother to “develop drive and do things on our own.” “My greatest fear as an entrepreneur is losing the hunger that got me here (referring to Samasource) and sparked my best ideas.”

(2) Submitting to consumerism: Photography is an art, not a product. It should tell a story, not record a moment. That is what Parris Whittingham, an entrepreneur behind his own studio that specializes in relationship photography (and incidentally snapped my profile photo) believes. He strives to tell love stories. He has to do so while also keeping his business in the black. In a competitive market, he says it’s easy to “sell something I don’t truly believe in,” meaning taking photographs that lack emotion or meaning; that are just superficial. “Losing my passion to capture the stories of the couples and people I’m photographing in order to stay in business terrifies me,” he says.

(3) Losing my reputation: Failing may be accepted in the United States, says Argentine entrepreneur Santi Bilinkis, but “failing in a Latin culture is very different.” Bilinkis who founded along with Andy Freire Officenet, Latin America’s Staples, says that “if you fail in the U.S., what matters most is the nature of your intentions and how much effort you put in…to some it may even be a plus, since they assume you have learned from that unsuccessful experience.” In Argentina, he says, “failing carries a huge stigma and may have long-lasting consequences (even legal!).” He says that what he “truly fears is ruining the most important asset” he has: his reputation. “That may very easily be destroyed by a single failed endeavor, despite honesty and hard work.”

(4) Losing my partners: Before Lebnan Nader launched a mobile gaming company, Birdy Nam Nam, in his native Lebanon, he made sure he had partners to do it with – not only to support him but to further the vision. Start-ups are not common in the Middle East and with Lebanon’s poor technology infrastructure, setting up an enterprise isn’t something to do alone. Nader persuaded his brother, Arz and a French-Lebanese techie JC Hoelt to join him.  “The first thing that encouraged us to move forward was the chemistry between us,” Nader says. “During the development and the launch of Birdy Nam Nam, we had a really good experience. Fun, enjoyable, smooth.” This is what he’s afraid of losing. “What scares me as an entrepreneur is losing the fun,” in order to focus on business.

(5) Becoming a business owner: Darcey Howard, brand strategist and founder of Personal Branding Through Appearance, is afraid of focusing so much on business that she stops being an entrepreneur and becomes a business owner. The brand strategist’s motto is  “do one thing that scares you everyday.” For her that one thing is becoming a better accountant, salesperson, marketer and manager. While those are necessary skills to run a business, Howard sees how they conflict with the “fluidity” of entrepreneurship. “I’m hardwired as an entrepreneur but not in love with being a business owner.” She knows that in order to succeed she has to submit to the later. “Did Superman ever get used to kryptonite?”

(6) Submitting to the negative: Entrepreneurs are known for their enthusiasm and unreasonable vision. Turkish entrepreneur Melek Pulatkonak says that doesn’t mean entrepreneurs aren’t human. The founder of Turkish Women’s International Network (of which I’m an advisory board member) she admits to worry. “I cannot share all of my worries with my team,” she says. Keeping them insider her, however, is something that scares her. “As Winston Churchill referenced, my success relies on my enthusiasm and running from one failure to another. I fear the day my inner well of positive energy runs dry.”

(7) Falling behind the innovation curve: What keeps Joe McMenemon up at night is “the knowledge that the competition may be working to catch up.” He is the co-founder of ChapterSpot, a web application that allows groups, mainly fraternities and sororities, communicate and share information. “Innovations and cool features are only an advantage until your competitors have replicated them on their platform. In the technology industry things move fast so you can never be satisfied with your current product,” he says. “It is essential to always be communicating with your clients and looking for new ways to improve their experience, even if sometimes you feel like you are competing against yourself.”

(8) Opportunity cost: Daniel MacCombie turned down “a potentially lucrative and intellectually rewarding career,” to start Runa, a social enterprise that buys guayusa from farmers in Ecuador and sells it in Western markets such as Whole Foods. Guayusa is a tree leaf “that has been brewed like tea” to offer “focused energy.” He says that he is scared of the opportunity cost of that trade off. “I have an obligation to make sure that in as much of what I do as I can manage, I am doing it in ways that I’m learning new skills, better understanding myself or taking lessons that can more broadly be applied in the rest of my life or in my future career, wherever that may lead,” MacCombie says.  At the same time he says, he is afraid that that focus won’t lead to the impact he wants Runa to have. “My company works to provide deep benefit to communities and ecosystems in Ecuador… I am always thinking about whether or not we are actually making that impact.”

(9) Losing my team: Every morning Jake Sigal, founder and CEO of Livio Radio, gets up, he makes sure that he has the “right attitude” and spreads his hard/play attitude throughout the office.” As a second-phase start-up based in Detroit that manufactures devices and software for Internet radio, he adds that he hopes the office “shows up” to experience it. “What scares me is coming into the office one morning and everyone quits,” says Sigal. That has made him conscientious of “treating people better than I expect to be treated.” “One of the main things I wanted to do when I started Livio was create a really cool and music oriented work environment.” But he says, “cool things in a company always open up the door for people to take advantage of the system.” Still, his Motown soul drives him to keep the team number one.

(10) Losing it all: Elizabeth Anne Frank, President of Eye-5, a modeling staffing agency, says that her biggest fear “is having to go back to work for someone else.” “If I ever had to return to a ‘normal’ work life, I would feel entirely and utterly defeated, like I failed at something so simple….I don’t think I could do it.”

Oh, I know what you mean Elli. Do I ever.

Happy Halloween.